Biocompatible flavonoid compounds for organelle and cell imaging

Abstract

Flavonoid compounds may be prepared that are selective for certain cell organelles, and may be used as biological imaging agents. Organelles that may be imaged with flavonoid compounds include mitochondria and lysosomes. Advantageously, the flavonoids show specificity to certain organelles and may exhibit a florescence “turn-on” mechanism, where the flavonoids that have target an organelle exhibit a florescence response when excited.

What is claimed is: 
     
       1. A flavonoid compound defined by the formula 
       
         
           
           
               
               
           
         
       
       where each R 1 -R 4  is individually an organic group or an hydrogen atom, R 5  and R 6  are each individually an organic group or an hydrogen atom or where R 5  and R 6  combine to form a single organic group, each R 7  is individually an organic group, and n is about 3 to 10 units. 
     
     
       2. The flavonoid of  claim 1 , where the flavonoid compound is defined by the formula 
       
         
           
           
               
               
           
         
       
       where each R 10 -R 4  is individually an organic group or an hydrogen atom, each R 7  is individually an organic group, and n is about 3 to 10 units. 
     
     
       3. The flavonoid of  claim 1 , where the flavonoid compound is defined by the formula 
       
         
           
           
               
               
           
         
       
       where n is about 3 to 10 units. 
     
     
       4. The flavonoid of  claim 1 , where the flavonoid compound is defined by the formula 
       
         
           
           
               
               
           
         
       
       where R 5  and R 6  are earch individually an organic group or an hydrogen atom or where R 5  and R 6  combine to form a single organic group and n is about 3 to 10 units. 
     
     
       5. A flavonoid compound defined by the formula 
       
         
           
           
               
               
           
         
       
       where each R 1 , R 3 , and R 4  is individually an organic group or an hydrogen atom, R 5  and R 6  are each individually an organic group or an hydrogen atom or where R 5  and R 6  combine to form a single organic group, R 8  is an organic group or a hydrogen atom, R 9  is an organic group or a hydrogen atom, R 11  and R 12  are each individually an organic group or an hydrogen atom or where R 11  and R 12  combine to form a single organic group, and n is about 1 to 6 units. 
     
     
       6. A method of imaging an organelle comprising
 combining a mitochondrion and a flavonoid compound and allowing the flavonoid compound to stain the mitochondrion, where the flavonoid compound is defined by the formula 
 
       
         
           
           
               
               
           
         
          where each R 1 -R 4  is individually an organic group or an hydrogen atom, R 5  and R 6  are each individually an organic group or an hydrogen atom or where R 5  and R 6  combine to form a single organic group, each R 7  is individually an organic group, and n is about 3 to 10 units; 
         irradiating the stained mitochondrion with an excitation wavelength that excites the flavonoid compound and induces a fluorescence response; and 
         capturing an image of the fluorescence response. 
       
     
     
       7. The method of  claim 6 , where the mitochondrion is an isolated cell-free mitochondrion. 
     
     
       8. The method of  claim 6 , where the mitochondrion is present in a eukaryotic cell. 
     
     
       9. The method of  claim 8 , where the eukaryotic cell is a stem cell. 
     
     
       10. The method of  claim 6 , where the step of allowing the flavonoid compound to stain the mitochondrion is performed by incubating a mitochondrion with about 0.02 μM to about 10 μM of the flavonoid compound at about 37° C. for about 25 min in a growth medium. 
     
     
       11. A method of imaging an organelle comprising
 combining a lysosome of a eukaryotic cell and a flavonoid compound and allowing the flavonoid compound to stain the lysosome, where the flavonoid compound is defined by the formula 
 
       
         
           
           
               
               
           
         
          where each R 1 , R 3 , and R 4  is individually an organic group or a hydrogen atom, R 5  and R 6  are each individually an organic group or a hydrogen atom or where R 5  and R 6  combine to form a single organic group, R 8  is an organic group or a hydrogen atom, R 9  is an organic group or a hydrogen atom, R 11  and R 12  are each individually an organic group or a hydrogen atom or where R 11  and R 12  combine to form a single organic group, and n is about 1 to 6 units; 
         irradiating the stained lysosome with an excitation wavelength that excites the flavonoid compound and induces a fluorescence response; and 
         capturing an image of the fluorescence response. 
       
     
     
       12. The method of  claim 11 , where the lysosome is an isolated cell-free lysosome. 
     
     
       13. The method of  claim 11 , where the lysosome is in a eukaryotic cell. 
     
     
       14. The method of  claim 13 , where the eukaryotic cell is a stem cell. 
     
     
       15. The method of  claim 11 , where the step of allowing the flavonoid compound to stain the lysosome is performed by incubating a lysosome with about 0.02 μM to about 10 μM of the flavonoid compound at about 37° C. for about 25 min in a growth medium.